DE1284420B - Verfahren zur Herstellung von ungesaettigten ª-Lactonen durch Dimerisieren von Ketenen - Google Patents
Verfahren zur Herstellung von ungesaettigten ª-Lactonen durch Dimerisieren von KetenenInfo
- Publication number
- DE1284420B DE1284420B DEE27922A DEE0027922A DE1284420B DE 1284420 B DE1284420 B DE 1284420B DE E27922 A DEE27922 A DE E27922A DE E0027922 A DEE0027922 A DE E0027922A DE 1284420 B DE1284420 B DE 1284420B
- Authority
- DE
- Germany
- Prior art keywords
- lactones
- lactone
- carbon atoms
- general formula
- unsaturated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002561 ketenes Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 230000000447 dimerizing effect Effects 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 5
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- -1 phosphorus compound Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical class CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- RGCDVHNITQEYPO-UHFFFAOYSA-N 2,2,4,4-tetramethylcyclobutane-1,3-dione Chemical compound CC1(C)C(=O)C(C)(C)C1=O RGCDVHNITQEYPO-UHFFFAOYSA-N 0.000 description 3
- GOXRESIYRAWNOJ-UHFFFAOYSA-N 3-hydroxy-2,2,4-trimethylpent-3-enoic acid Chemical compound CC(C)=C(O)C(C)(C)C(O)=O GOXRESIYRAWNOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- YBAAIJIDIRQVLY-UHFFFAOYSA-N dibutoxy(phenyl)phosphane Chemical compound CCCCOP(OCCCC)C1=CC=CC=C1 YBAAIJIDIRQVLY-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003003 phosphines Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DAMMCOFPNDKYBA-UHFFFAOYSA-N 1,3-dioxocane-4,8-dione Chemical class O=C1CCCC(=O)OCO1 DAMMCOFPNDKYBA-UHFFFAOYSA-N 0.000 description 1
- NFRJJFMXYKSRPK-ONEGZZNKSA-N 2-Methyl-3-pentenoic acid Chemical compound C\C=C\C(C)C(O)=O NFRJJFMXYKSRPK-ONEGZZNKSA-N 0.000 description 1
- BOJMIFVSWVYHBX-UHFFFAOYSA-N 2-butyl-2,4-diethyl-3-hydroxyoct-3-enoic acid Chemical compound C(CCC)C(C(=O)O)(C(=C(CCCC)CC)O)CC BOJMIFVSWVYHBX-UHFFFAOYSA-N 0.000 description 1
- NWXORMWIWGSYJJ-UHFFFAOYSA-N 2-ethylbut-1-en-1-one Chemical compound CCC(CC)=C=O NWXORMWIWGSYJJ-UHFFFAOYSA-N 0.000 description 1
- YBXJZGOTBMPKNO-UHFFFAOYSA-N 2-ethylhex-1-en-1-one Chemical compound CCCCC(CC)=C=O YBXJZGOTBMPKNO-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SOURFCQONLGLPA-UHFFFAOYSA-N P([O-])([O-])[O-].[C+4].P([O-])([O-])[O-].P([O-])([O-])[O-].P([O-])([O-])[O-].[C+4].[C+4] Chemical class P([O-])([O-])[O-].[C+4].P([O-])([O-])[O-].P([O-])([O-])[O-].P([O-])([O-])[O-].[C+4].[C+4] SOURFCQONLGLPA-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- APANVIDUYWAGRG-UHFFFAOYSA-N butyl-dihydroxy-diphenyl-lambda5-phosphane Chemical compound C=1C=CC=CC=1P(O)(O)(CCCC)C1=CC=CC=C1 APANVIDUYWAGRG-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical compound CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US321280A US3234241A (en) | 1963-11-04 | 1963-11-04 | Process for preparing 2, 2, 4, 4-tetraalkyl-3-hydroxy-3-butenoic acid beta-lactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1284420B true DE1284420B (de) | 1968-12-05 |
Family
ID=23249947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEE27922A Pending DE1284420B (de) | 1963-11-04 | 1964-10-09 | Verfahren zur Herstellung von ungesaettigten ª-Lactonen durch Dimerisieren von Ketenen |
Country Status (4)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114853606B (zh) * | 2022-06-18 | 2023-09-29 | 衢州伟荣药化股份有限公司 | 一种乙酸异丙烯酯的制备方法 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2450133A (en) * | 1947-07-12 | 1948-09-28 | Eastman Kodak Co | Process for preparing lactones |
| US2675372A (en) * | 1952-07-09 | 1954-04-13 | Eastman Kodak Co | Polymerization of monomeric vinyl compounds |
| US3027359A (en) * | 1959-06-19 | 1962-03-27 | Jurgeleit Hans Wolfgang | Tertiary phosphine polymerization catalysts system |
| US3062837A (en) * | 1962-11-06 | Method of preparing | ||
| US3074999A (en) * | 1958-12-31 | 1963-01-22 | American Cyanamid Co | Preparation of dialkyl 2-methyleneglutarates |
| FR1321323A (fr) * | 1962-05-07 | 1963-03-15 | Eastman Kodak Co | Nouvelles bêta-lactones et procédé pour leur préparation |
| US3089896A (en) * | 1963-05-14 | Preparation of enolates of | ||
| FR1366081A (fr) * | 1963-05-24 | 1964-07-10 | Rhone Poulenc Sa | Dicyano-2, 4 butène-1 |
| US3161656A (en) * | 1961-05-09 | 1964-12-15 | Eastman Kodak Co | Unsaturated beta-lactones and method of preparing them |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3062836A (en) * | 1961-05-09 | 1962-11-06 | Eastman Kodak Co | Method of preparing beta-lactones of 2, 2, 4, 4-tetraalkyl-3-hydroxy-3-butenoic acids by catalyzed reaction of dialkylketenes |
-
0
- BE BE655214D patent/BE655214A/xx unknown
-
1963
- 1963-11-04 US US321280A patent/US3234241A/en not_active Expired - Lifetime
-
1964
- 1964-10-09 DE DEE27922A patent/DE1284420B/de active Pending
- 1964-11-04 GB GB44903/64A patent/GB1086006A/en not_active Expired
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3062837A (en) * | 1962-11-06 | Method of preparing | ||
| US3089896A (en) * | 1963-05-14 | Preparation of enolates of | ||
| US2450133A (en) * | 1947-07-12 | 1948-09-28 | Eastman Kodak Co | Process for preparing lactones |
| US2675372A (en) * | 1952-07-09 | 1954-04-13 | Eastman Kodak Co | Polymerization of monomeric vinyl compounds |
| US3074999A (en) * | 1958-12-31 | 1963-01-22 | American Cyanamid Co | Preparation of dialkyl 2-methyleneglutarates |
| US3027359A (en) * | 1959-06-19 | 1962-03-27 | Jurgeleit Hans Wolfgang | Tertiary phosphine polymerization catalysts system |
| US3161656A (en) * | 1961-05-09 | 1964-12-15 | Eastman Kodak Co | Unsaturated beta-lactones and method of preparing them |
| FR1321323A (fr) * | 1962-05-07 | 1963-03-15 | Eastman Kodak Co | Nouvelles bêta-lactones et procédé pour leur préparation |
| FR1366081A (fr) * | 1963-05-24 | 1964-07-10 | Rhone Poulenc Sa | Dicyano-2, 4 butène-1 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE655214A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| US3234241A (en) | 1966-02-08 |
| GB1086006A (en) | 1967-10-04 |
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